This episode of the Legend Makers Podcast features Jeffrey Riley, former Massachusetts Commissioner of Elementary and Secondary Education and current leader at Day of AI, a nonprofit launched out of MIT. After more than three decades in public education, Jeff believes AI can usher in a new era of learning if schools use it wisely and protect what must remain human in the classroom.

Scott and Jeff discuss the promise and risks of AI, the lessons learned from the rise of social media, and why educators must establish boundaries and policies that keep students safe. Jeff explains how AI can help teachers personalize instruction, reduce administrative burdens, and reclaim the creative work that drew them into teaching.

If you want a clear, practical, and honest look at how AI will shape the future of teaching and learning, this episode provides essential insight.

In this episode, you will learn:

• How Jeffrey’s journey from Teach For America teacher to state commissioner shaped his views on equity and opportunity.

• Why he believes the country mishandled the social media era and how those mistakes should guide AI adoption.

• How Day of AI trains teachers and administrators, assists districts with policy, and builds AI literacy curriculum for students.

• What true personalization looks like with AI, including practical classroom examples.

• Why AI will not replace teachers and how it can instead restore time for lesson design, creativity, and student engagement.

• The policy questions schools must confront, including student data privacy, academic integrity, and the limits of surveillance tools.

• How to teach students AI literacy through simple, hands-on lessons that build precision, reasoning, and safe usage habits.

• Why foundational skills like writing, thinking, and spatial awareness must remain part of a student’s education even as AI advances.

• Why Jeff believes AI can bring joy back to classrooms, reduce burnout, and draw more people into the profession.

About Jeffrey Riley

Jeffrey Riley spent 32 years in public education as a teacher, principal, receiver of Lawrence Public Schools, and Commissioner of Elementary and Secondary Education in Massachusetts. At Day of AI, he works with MIT technologists and veteran educators to help schools implement AI safely and effectively. Learn more at dayofai.org or connect with him on LinkedIn.

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